4-Formylbenzoic acid → 4-formyl-N-{3-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)-2-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]propyl}benzamide

HRID 539401Notes

Reaction equation

HRID 539401 reaction equation
[CH3:1][Si:2]([CH3:31])([CH3:30])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH2:12][CH:13]([CH2:16][C:17]1[N:18]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:19]=[CH:20][N:21]=1)[CH2:14][NH2:15].[CH:32]([C:34]1[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=1)=[O:33].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=C1>O.CN(C)C=O>[CH:32]([C:34]1[CH:42]=[CH:41][C:37]([C:38]([NH:15][CH2:14][CH:13]([CH2:16][C:17]2[N:18]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:28])([CH3:27])[CH3:29])[CH:19]=[CH:20][N:21]=2)[CH2:12][C:8]2[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:30])[CH3:31])[CH:11]=[CH:10][N:9]=2)=[O:39])=[CH:36][CH:35]=1)=[O:33]

Participants

7

Reactant 4

HCID 120884-Formylbenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 5764791-HydroxybenzimidazoleHCID 689568283-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)-2-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]-1-propanamine

Product 1

HCID 866301034-formyl-N-{3-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)-2-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]propyl}benzamideYield 132.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a dimethylformamide (2 mL) solution of the compound (300 mg) produced in Example 29 and 4-formylbenzoic acid (116 mg), 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide (hereafter abbreviated to EDC) (274 mg) and 1-hydroxybenzimidazole (104 mg) were added in this order. The reaction solution was stirred at room temperature for 17 hour. To the reaction solution, water (10 mL) was added. The aqueous layer was extracted twice with dichloromethane (20 mL). The combined organic layer was washed with saturated sodium chloride solution (20 mL) and then dried over anhydrous magnesium sulfate. After removing the anhydrous magnesium sulfate by filtration, the filtrate was concentrated. The residue was purified by silica gel chromatography (ethyl acetate:methanol:28% aqueous ammonia=1:0:0→100:10:1) to obtain the title compound (510 mg).

Workup

  1. extractionThe aqueous layer was extracted twice with dichloromethane (20 mL)
  2. washThe combined organic layer was washed with saturated sodium chloride solution (20 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing the anhydrous magnesium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel chromatography (ethyl acetate:methanol:28% aqueous ammonia=1:0:0→100:10:1)

Sources & evidence

ORD record
ord-159b2fadd00446799801319c4bf5b1ef
Source dataset
uspto-grants-2014_10
Patent number
US08871210B2

Reaction notes

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